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PubMed1982

Limitations of the sodium fusion assay for fluorinated metabolites.

A method involving sodium fusion and analysis by fluoride electrode, which has been used for the determination of total fluorinated metabolites of fluorine-containing drugs in physiologic fluids, is shown to be inapplicable to volatile fluorinated metabolites of volatile fluorinated anesthetic agents. The yields of inorganic fluoride from the volatile metabolites 2,2,2-trifluoroethanol and trifluoroacetaldehyde were less than 2% of expected values, whether these metabolites were present in water, buffer, urine, or hepatic microsomes, although reliable results were obtained for the relatively nonvolatile sodium trifluoroacetate. It is proposed that the assay does not provide a valid method for determining total fluorinated metabolites of volatile or nonvolatile fluorine-containing drugs, but may be of some use in determining a single nonvolatile fluorinated metabolite of a volatile fluorinated drug.

Anesthetics↗
PubMed2003

Fluorinated matrix approach for the characterization of hydrophobic perfluoropolyethers by matrix-assisted laser desorption/ionization time-of-flight MS.

Characterization of fluorinated polymers in MALDI is often unsuccessful because commonly used matrixes, such as 2,5-dihydroxybenzoic acid, Indole acrylic acid, alpha-cyano-4-hydroxycinnamic acid, etc., do not desorb/ionize fluorinated polymers efficiently. This could be in part attributed to the unfavorable interaction between the matrix molecules and fluorinated oligomers due to differences in their hydrophobicities. Moreover, the relative cation affinity between the matrix molecules and the fluorinated oligomers may not favor the gas-phase cationization process of the fluorinated oligomers. To overcome these limitations, fluorinated derivates of benzoic acid (pentafluorobenzoic acid) and cinnamic acid (Pentafluoro cinnamic acid) were employed for the desorption/ionization of perfluoropolyethers. Presence of fluorine atoms in the matrix might improve the interaction between the matrix and perfluoroether during the crystallization or ionization step. With a pentafluorobenzoic acid matrix, intact silver cationized oligomers were desorbed, whereas with a pentafluorocinnamic acid matrix, loss of end group was observed. This loss could be rationalized by the dissociation of the silver cationized oligomers via an ion-dipole mechanism. This work shows the possibility of characterizing yet another important class of fluorinated polymer by MALDI-TOFMS.

Journal Article↗
PubMed2006

Quantitative determination of fluorinated alkyl substances by large-volume-injection liquid chromatography tandem mass spectrometry-characterization of municipal wastewaters.

A quantitative method was developed for the determination of fluorinated alkyl substances in municipal wastewater influents and effluents. The method consisted of centrifugation followed by large-volume injection (500 microL) of the supernatant onto a liquid chromatograph with a reverse-phase column and detection by electrospray ionization and tandem mass spectrometry. The fluorinated analytes studied include perfluoroalkyl sulfonates, fluorotelomer sulfonates, perfluorocarboxylates, and select fluorinated alkyl sulfonamides. Recoveries of the fluorinated analytes from wastewater treatment plant (WWTP) raw influents and final effluent were in the ranges of 82-100% and 86-100%, respectively. The lower limit of quantitation was 0.5 ng/L depending on the analyte. The method was applied to flow-proportional composites of raw influent and final effluent collected over a 24 h period from 10 WWTPs nationwide. Fluorinated alkyl substances were observed in wastewater at all treatment plants, and each plant exhibited unique distributions of fluorinated alkyl substances despite similarities in treatment processes. In 9 out of the 10 plants sampled, at least one class of fluorinated alkyl substances exhibited increased concentrations in the effluent as compared to the influent concentrations. In some instances, decreases in certain fluorinated analyte concentrations were observed and attributed to sorption to sludge.

Alkanesulfonic Acids↗
PubMed2006

Atomic and electronic structures of fluorinated BN nanotubes: computational study.

The atomic and electronic structures of fluorinated BN nanotubes (BNNTs) were investigated by generalized gradient approximation (GGA) density functional theory (DFT). The reaction energies of F2 with pristine single-walled BNNTs to form fluorinated BNNTs are exothermic up to 50% coverage. At lower F coverages (below 50%), fluorines prefer external attachments to boron atoms and stay as far away as possible. At 50% F coverage, fluorines favor attachment to all the boron atoms of the outer surface energetically. Such preferable fluorination patterns and highly exothermic reaction energies hold true for double-walled (and multiwalled) BNNTs when the outer tube surface is considered. Fluorination transforms BNNTs into p-type semiconductors at low F coverages, while high F coverages convert BNNTs into p-type conductors. Therefore, the electronic and transport properties of BNNTs can be engineered by fluorination, and this provides potential applications for fluorinated BNNTs in nanoelectronics.

Journal Article↗
PubMed2004

Ab initio calculations to model anomalous fluorine behavior.

Implanted fluorine is observed to behave unusually in silicon, manifesting apparent uphill diffusion and reducing diffusion and enhancing activation of boron. In order to investigate fluorine behavior, we calculate the energy of fluorine defect structures in the framework of density functional theory. In addition to identifying the ground-state configuration and diffusion migration barrier of a single fluorine atom in silicon, a set of energetically favorable fluorine defect structures were found (F(n)V(m)). The decoration of vacancies and dangling silicon bonds by fluorine suggests that fluorine accumulates in vacancy-rich regions, which explains the fluorine redistribution behavior reported experimentally.

Journal Article↗
PubMed2004

Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles induce CYP1A1 expression, become metabolized, and bind to macromolecules in sensitive human cancer cells.

Fluorinated 2-(4-amino-3-methylphenyl)benzothiazoles possess potent antiproliferative activity against certain cancer cells, similar to the unfluorinated 2-(4-amino-3-methylphenyl)benzothiazole (DF 203, NSC 674495). In "sensitive" cancer cells, DF 203 is metabolized by, can induce expression of, and binds covalently to CYP1A1. Metabolism appears to be essential for its antiproliferative activity through DNA adduct formation. However, a biphasic dose-response relationship compromises its straightforward development as a chemotherapeutic agent. We investigated whether fluorinated benzothiazoles inhibit cancer cell growth without the biphasic dose-response, and whether the fluorinated benzothiazoles are also metabolized into reactive species, with binding to macromolecules in sensitive cancer cells. One fluorinated benzothiazole, 2-(4-amino-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) did exhibit potent, antiproliferative activity without a biphasic dose-response. The fluorinated benzothiazoles were also metabolized only in cells, which subsequently showed evidence of cell death. We used microsomes from genetically engineered human B-lymphoblastoid cells expressing cytochromes P450 (CYP1A1, CYP1A2, or CYP1B1) to clarify the basis for fluorinated benzothiazole metabolism. 5F 203 induced CYP1A1 and CYP1B1 mRNA expression in sensitive breast and renal cancer cells, whereas 5F 203 induced CYP1A1 mRNA but not CYP1B1 mRNA expression in sensitive ovarian cancer cells. 5F 203 did not induce CYP1A1 or CYP1B1 mRNA expression in any "resistant" cancer cells. The fluorinated benzothiazoles induced CYP1A1 protein expression exclusively in sensitive cells. [14C]5F 203 bound substantially to subcellular fractions in sensitive cells but only minimally in resistant cells. These data are concordant with the antiproliferative activity of fluorinated benzothiazoles deriving from their ability to become metabolized and bind to macromolecules within sensitive cells.

Antineoplastic Agents↗
PubMed2004

Modern synthetic methods for fluorine-substituted target molecules.

Fluorine has come to be recognized as a key element in materials science: in heat-transfer agents, liquid crystals, dyes, surfactants, plastics, elastomers, membranes, and other materials. Furthermore, many fluorine-containing biologically active agents are finding applications as pharmaceuticals and agrochemicals. Progress in synthetic fluorine chemistry has been critical to the development of these fields and has led to the invention of many novel fluorinated molecules as future drugs and materials. As a result of the electronic effects of fluorine substituents, fluorinated substrates and reagents often exhibit unusual and unique chemical properties, which often make them incompatible with established synthetic methods. Thus, the problem of how to control the unusual properties of compounds with fluorine substituents deserves much attention, so as to promote the design of facile, efficient, and environmentally benign methods for the synthesis of valuable organofluorine targets.

Chemistry, Agricultural↗
PubMed1994

Content of fluorine in vegetables and fruits from an industrial area.

Content of fluorine in vegetables and fruits from allotments situated in an industrial area as well as in an agricultural area without industrial emissions was determined. The fluorine determination was made by means of a potentiometric method with application of an ion-selective electrode. Statistically significant differences between the fluorine content in vegetables and fruits from an area contaminated with the emissions of fluorine compounds and the fluorine content in vegetables and fruits from the control area were found. Significant differences between the fluorine content in above- and under-ground parts of some vegetables were stated. The greatest fluorine content appeared in parsley haulm and in black currants.

Fluorine↗
PubMedDate not supplied

In vivo fluorine-19 MR imaging: relaxation enhancement with Gd-DTPA.

The lack of a naturally occurring background signal from fluorine in magnetic resonance (MR) imaging makes fluorinated compounds potentially attractive candidates for tissue-specific MR contrast agents. Problems associated with the in vivo use of fluorinated compounds are toxicity, which limits the amount of agent that can be used; multiple resonance lines; and an excessively long T1, which leads to long sequence TRs and consequently long imaging times. Many fluorinated agents also possess complex MR spectra that result in chemical shift artifacts if not corrected. The authors demonstrate the use of an extracellular fluorinated agent with a single MR peak for selective imaging of a brain abscess in an animal model and show that the image signal per unit of acquisition time can be enhanced through the use of a T1 relaxation agent, gadolinium diethylenetriamine-pentaacetic acid (DTPA). Trifluoromethylsulfonate was administered at a fluorine-19 dose of 4 mmol/kg, and fluorine images of the induced abscess were acquired before and after the injection of a standard dose of Gd-DTPA (0.1 mmol/kg); non-section-selected projection images were used. Typical imaging times were less than 5 minutes. The signal enhancement factor achieved was approximately four (4.0 +/- 0.8) with use of a 500/12 (TR msec/TE msec) spin-echo sequence.

Animals↗
PubMed2005

Dental caries in fluorine exposure areas in China.

In this study, fluorine concentrations in drinking water and in urine of residents from a fluorine exposure area in China were tested. DMFT (average number of decayed, missing and filled teeth) of local residents in four age groups were also determined. The results of the study indicate that in fluorine exposure areas, there is a strictly positive correlation between fluorine content in urine and the fluorine content in drinking water. Effect of dental caries by high fluorine content drinking water is different for the different age groups. High fluorine content drinking water is more dangerous for 15-and 18-year-old groups than 5- and 12-year-old groups.

Adolescent↗
PubMed1994

Fluorinated phosphatidylcholine-based liposomes: H+/Na+ permeability, active doxorubicin encapsulation and stability, in human serum.

The active encapsulation of doxorubicin (DOX) into fluorinated liposomes, the stability of these liposomes with respect to encapsulated DOX release in buffer and in human serum, and their H+/Na+ membrane permeability have been investigated and compared to those of their conventional hydrogenated analogues. These fluorinated liposomes are made from highly fluorinated phosphatidylcholines and contain a fluorinated core within their membrane. We found that the presence of this fluorinated core is not a barrier for the active encapsulation of DOX. Efficient (> 90%) and stable loading could be achieved using a transmembrane ammonium sulfate or even, in the absence of Na+, a transmembrane pH gradient. The higher H+/Na+ permeability found for the fluorinated membranes, as compared to conventional ones, is responsible for the lower stability observed for the DOX-loaded fluorinated liposomes when incubated in a physiological buffer (PBS) or in human serum. It is also noticeable that the retention of DOX is increased in human serum and for the liposomes whose membranes are in a gel or in a semi-fluid semi-gel state at 37 degrees C.

Doxorubicin↗
PubMed2001

Processing procedures of brick tea and their influence on fluorine content.

China is the only country that produces brick tea, and more than 90% of the brick tea is consumed in the western minority nationality regions of China. The high fluorine content of brick tea is possibly associated with the special processing procedures, but no investigation has been conducted in this field. To explore the characteristic features of brick tea manufacturing and the alterations in fluorine content during the processing procedures, we performed a field survey involving two brick tea factories and the nearby tea plantations. For the fluorine contents of the initial, intermediate and final processing products, altogether eight types of specimens were collected and determined by using the ion-selective electrode standard curve technique. It was found that the raw material tea leaf for brick tea processing was old, coarse and not the tender delicate tea leaf used for ordinary green or black tea processing. For the fluorine content of the raw material tea leaf, the intermediate and the final products showed that the fresh raw leaf contained a fluorine content as high as 489.31-512.68 mg/kg. During one fermentation-like processing procedure, the fluorine content rose by 4.67% and 1.88% in the specimens from the two factories, respectively, which revealed no statistical significance (P>0.5). These results suggest that the high fluorine content in brick tea might be due to the high content in the raw material and not related with the processing procedures.

China↗
PubMed1998

Safety evaluation and fluorine concentration of Pu'er brick tea and Bianxiao brick tea.

Pu'er brick tea and Bianxiao brick tea are both compressed types of tea. Fluorine analysis was carried out on samples of Pu'er brick tea produced at different times in Yunnan Province and on samples of Bianxiao brick tea made in Hunan and Sichuan Province for supply especially to minority ethnic groups in border areas of China. The levels of water-soluble and water-insoluble fluorine were measured in the tea samples using an ion-specific electrode potentiometer. The concentration of water-soluble fluorine was much greater in Bianxiao brick tea than in Pu'er brick tea (mean levels 441 and 77 mg/kg, respectively). According to these figures, the fluorine intake associated with consuming an infusion of 30 g Pu'er brick tea/person/day is safe because it does not exceed the maximum recommended daily allowance (RDA) of up to 4.0 mg for adults. In contrast, the almost six times higher intake of fluorine from Bianxiao brick tea greatly exceeds the 4 mg RDA and is unsafe. The difference in the fluorine levels of the two types of brick tea can be attributed to differences in the materials used to make them: Pu'er brick tea is made from tender leaves whereas Bianxiao brick tea is made from old tough leaves in which fluorine has accumulated. We conclude that consumption of Pu'er brick tea is unlikely to induce fluorosis, which has been associated with consumption of Bianxiao brick tea.

Fluorine↗
PubMedDate not supplied

Fluorinated proteins as potential 19F magnetic resonance imaging and spectroscopy agents.

Fluorinated proteins have been synthesized and characterized as potential in vivo 19F magnetic resonance imaging (MRI) and spectroscopy (MRS) agents. Proteins labeled with fluorine include bovine serum albumin, gamma-globulin, and purified immunoglobulin (IgG). The amino groups in proteins were selectively trifluoroacetylated using S-ethyl trifluorothioacetate to synthesize fluorinated proteins (TFA-protein; 1-3). In another approach, trifluoroacetamidosuccinic anhydride has been used to prepare corresponding fluorinated derivatives of proteins (TFASA-protein; 4-6). The fluorinated proteins have been purified by exhaustive dialysis and isolated in good yields (55-76%). The fluorinated proteins exhibit useful NMR characteristics and the biocompatibility for in vivo studies. The initial investigations demonstrate the potential of these new fluorinated proteins as in vivo MRI/MRS probes.

Animals↗
PubMed2005

Structural and spectral response of Aequorea victoria green fluorescent proteins to chromophore fluorination.

Global replacements of tyrosine by 2- and 3-fluorotyrosine in "enhanced green" and "enhanced yellow" mutants of Aequorea victoria green fluorescent proteins (avGFPs) provided protein variants with novel biophysical properties. While crystallographic and modeled structures of these proteins are indistinguishable from those of their native counterparts (i.e., they are perfectly isomorphous), there are considerable differences in their spectroscopic properties. The fluorine being an integral part of the avGFP chromophore induces changes in the titration curves, variations in the intensity of the absorbance and fluorescence, and spectral shifts in the emission maxima. Furthermore, targeted fluorination in close proximity to the fluorinated chromophore yielded additional variants with considerably enhanced spectral changes. These unique spectral properties are intrinsic features of the fluorinated avGFPs, in the context of the rigid chromophore-microenvironment interactions. The availability of the isomorpohous crystal structures of fluorinated avGFPs allowed mapping of novel, unusual interaction distances created by the presence of fluorine atoms. In addition, fluorine atoms in the ortho position of the chromophore tyrosyl moiety exhibit a single conformation, while in the meta position two conformer states were observed in the crystalline state. Such global replacements in chromophores of avGFPs and similar proteins result in "atomic mutations" (i.e., H --> F replacements) in the structures, offering unprecedented opportunities to understand and manipulate the relationships between protein structure and spectroscopic properties.

Animals↗
PubMed2006

Alpha-helix formation in melittin and beta-lactoglobulin A induced by fluorinated dialcohols.

Extensive study of the effect of fluorinated alcohols on protein conformations, notably the induction of alpha-helix formation, is important because of its wide range of applications. Circular dichroism (CD) was used to show that the enhancement of helix induction in beta-lactoglobulin A and melittin by the fluorinated diols 2,2,3,3-tetrafluoro-1,4-butanediol (TFBD), 2,2,3,3,4,4-hexafluoro-1,6-pentanediol (HFPD), and 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (OFHD) increases in the order TFBD < HFPD < OFHD. For fluorinated diols and monoalcohols the effectiveness of helix induction was found to increase exponentially with increasing number of fluorine atoms per alcohol molecule, and OFHD was found to be more effective than any previously reported fluorinated alcohol. Formation of standard micelles was ruled out as the cause of the enhanced helix induction by the fluorinated diols. The negligible red-edge excitation shift in the fluorescence of melittin indicated that the fluorinated diol/water solvent shell surrounding the tryptophan chromophore is less immobilized than are molecules in a lamellar vesicle.

Alcohols↗
PubMed1990

Evaluation of analytical methods for fluorine in biological and related materials.

During the past two decades, some major pitfalls in fluorine analysis have been recognized and overcome. Therefore, it is important that facts be separated from fallacies in published literature on levels and forms of fluorine (ionic, bound, covalent, etc.) in biological materials, in order that correct perceptions of physiological, biochemical, and toxicological aspects of inorganic as well as organic fluorine compounds can be formed. Trace amounts of inorganic fluoride in biological samples can now be accurately determined with the fluoride electrode either directly or following diffusion, adsorption, or reverse extraction of fluoride (when necessary). The aluminum monofluoride molecular absorption technique provides an excellent rapid method for determination of trace amounts of inorganic fluoride (in the absence of organic fluorine). Fluorine in most organic fluorine compounds is not available for distillation, diffusion, or reverse-extraction. The sample needs to be ashed (open ashing) or combusted (oxygen flask, oxygen bomb, pyrohydrolysis) for covalently bound fluorine to be converted to fluoride ions. This can now be readily accomplished at room temperature by the reductive cleavage of the C-F bond with the sodium biphenyl reagent. Some recommendations for future research have been made.

Animals↗
PubMed1989

Micro-PIGE determination of fluorine distribution in developing hamster tooth germs.

A micro-PIGE (Proton-Induced gamma-ray Emission) technique based on the delayed 5/2+----1/2+ nuclear transition of fluorine (E gamma = 197 keV, t1/2 = 87 ns) emitted after 19F(p,p', gamma)19F reaction was used to detect and study the distribution of fluorine in the developing enamel organ during pre-eruptive stages, i.e., the transitional to early maturation stages of enamel formation in neonatal hamsters administered a single IP dose of sodium fluoride (20 mg NaF/kg body weight). The aforementioned nuclear reaction is unique for fluorine, and therefore detection of gamma-rays emanating from this reaction in a biological specimen implies a positive identification of fluorine at that particular site. Calcium and phosphorus X-rays were also recorded and used as parameters for assessment of the relationship between the degree of mineralization and fluoride incorporation into the enamel organ. The highest fluorine concentration in the enamel organ was recorded in the dentin near the dentin-enamel junction (DEJ). In the enamel, the highest concentration of fluorine was found to be associated with the more mature areas of the enamel near the DEJ, but gradually decreased in the direction of the enamel surface. Fluorine was not detected in the control germs. These results suggest that administration of fluoride in high doses during the pre-eruptive stages of enamel formation leads to incorporation of the ion into the forming dentin and enamel mineral, and that the enamel matrix does not seem to bind fluoride avidly.

Animals↗